Ad Men: Hell and Back
by BRyder27
Summary: Jeremy Gilbert is a recent college grad looking for a real job. He never expects for his first job as the secretary for the creative director of Betancourt and Sherman to change his life so dramatically. Especially when that creative director is the demanding and brash, Damon Salvatore. Slash D/J. AU- all human
1. Chapter 1

**A/N: Hi, I am back! All of you probably remember me from Sparked Interests. Here I am with another Damon/Jeremy fic and it's inspired by my current obsession with Mad Men. This story is inspired by an episode in S2 where Don tells Joan to find him another secretary.. one that can effectively manage his life and reputation. They didn't really expand on that much.. so I took the idea and this happened. This fic does not take place in the 60's like Mad Men does. There will be no Mad Men characters making an appearance as this is not a cross over. This is modern and is slash so if you haven't read by me before a lot of my TVD work is slash meaning male/male pairings. There may be a bit of het in this though so be warned about that. Updates are most likely going to be slow.. I have a job and graduate college in a few months so this is a busy time for me. But this story needed to be written and I hope you all will enjoy it! Feedback will be greatly appreciated. Also, Damon's character in this story will be highly similar to Don Draper. My obsession with Don Draper is partly what spurred this on. The TVD characters will be similar to how they are on the show but some of them may be different like Elena and Matt for example. **

**Disclaimer: I do not own The Vampire Diaries or Mad Men. **

The agency of Betancourt and Sherman is the top advertising firm in Richmond, Virginia. Jeremy Gilbert is a recent graduate of UVA with a degree in marketing. Fresh out of college with no internship or experience makes finding a decent job challenging. He committed to leaving his retail job so he had to make it work. He applied for entry level positions hoping to get a bite from an employer so he could move to his own place away from the small town and his overbearing sister. Their parents passed away when they were young and his sister, Elena, took custody of him. He didn't get the typical college experience of living on campus and had to commute to his classes. Needles to say, he wanted to land a great job and start making his own way in the world.

Which was why he was so surprised when there was a job posting for a secretary to the creative director of the Betancourt Sherman agency. The posting called for someone able to mingle in all types of social situations, deal with the clients, handle the schedule and anticipate the needs of his boss. Granted, it sounded like a female position, but this wasn't the fifties anymore. The position could turn into an actual advertising position if he played his cards right. He immediately sent off his resume and cover letter, filled with hope. Next, he pulled open Google and searched for information about the agency's staff. The creative director, Damon Salvatore, was 35 years old with a degree from Stanford and an eye for advertising. He came to Virginia from an agency in Los Angeles who merged with Betancourt and Sherman. The article wasn't what had Jeremy in shock.

It was the business picture included. The man was a sight for sore eyes and had the bluest eyes and blackest hair he had ever seen. Not to mention his face was one created by God himself. The way he was posed in the picture sent off an air of total control and confidence. Jeremy knew he had to do everything in his power to get this job. If not no other reason than to stare at that gorgeous face every day. Coming out had never been an option for him. His sister, Elena, was a debutante which meant how he lived reflected on her and her standing within the community. He dated one of her friends, Bonnie, but it became too difficult to keep up the ruse and physically please her. Therefore he had to end the relationship and blamed his career for the break up.

Elena wasn't too thrilled that she had a broken hearted best friend to console. But, she understood his reasoning. He was ready to get out from underneath his sister and her expectations. She'd be fine without him since she had her boyfriend, Matthew Donovan, the son of a stock broker. Matt could be pretentious at times, but there was no doubt he loved Elena and could take care of her. He wanted to be there for her. It was hard to when he couldn't sort himself out. Right then, he promised himself that he would come back to take care of her when he finished his self discovery. He closed his lap top and rose from his chair, going to his closet to change into workout clothes to hit the gym. While he shed his sweater, his phone started blaring music. He ran to his desk and answered it.

"Hello?"

"I'm looking to speak with a Jeremy Gilbert."

"This is him."

"Mr. Gilbert, this is Hilary Joyner from Betancourt and Sherman. Are you available to come in for an interview next week?" asked the professional sounding woman.

Jeremy almost dropped his phone in shock. They were quick in getting back with him. "Yes ma'am. When do I need to come in?"

"How's Tuesday at one o'clock?"

"Sounds great."

"When you arrive, come to the fourth floor and you'll see my desk when you first walk in and I'll escort you to Mr. Salvatore's office for the interview."

"Yes ma'am, thank you," replied Jeremy, hanging up.

His heart started racing and he had no idea how he'd make it through an interview with Mr. Sexy Salvatore.


	2. Chapter 2

Richmond was a two hour drive from Mystic Falls. Which meant Jeremy had to leave earlier to make sure he found the building and where he was supposed to go. For his outfit, he chose to wear a light pink button up shirt, a blue bow tie, black slacks and a matching black sport coat. Well dressed and self assured were the two qualities he wanted to project with his image. First impressions meant everything and he was determined not to let nerves get the best of him. Elena wished him good luck and he knew he had to get on the road or he'd be late.

Reality didn't set in until he reached the Richmond city limits. Traffic was heavy, but he managed to navigate his way through it. The building of Betancourt and Sherman was housed in stood at ten stories with a downtown location. He parked his car in the visitor's spot and checked his reflection before making his way into the tall grey building. There were people going in and out of the building and it made Jeremy wonder what other businesses resided inside. He took a deep breath and followed the stream of people inside the elevator. The number four was already lit up, so he patiently waited until it was his turn to get off. A lady beside him cried quietly into a tissue and he hoped his interview didn't end with him upset.

The elevator finally reached the fourth floor and he strode out to a set a glass doors with the words Betancourt and Sherman frosted over them. As he walked in, there was a reception area and further out there were desks situated in front of office doors. Once he got to reception, he was greeted by a striking woman wit perfectly cut short brown hair and a suit that could only be Chanel.

"Mr. Gilbert?" she questioned, standing up and smiling.

"Yes, ma'am. Ms. Hilary, right?" he asked, shaking her hand.

"Yes, come right this way and I'll show you how it works. Mr. Salvatore had me schedule all the interviews at this time. He'll make his decision today and go through the list until he finds the best fit. This is the second round of interviews. Have a seat and I'll call you when he's ready to see you. Good luck," explained Hilary, leading him to the waiting area.

The fact that it was the second round of interviews scared him a little. It meant Mr. Salvatore was either a total dick or extremely picky. He sat down and subtly eyed his competition which seemed to be primarily women. The only advantage they had over hi was their tits and legs showing from underneath their skirts. But, he had skills and confidence that would hopefully land him the job. The air around him reeked of French perfume, most likely Dior or Chanel. He lightly dabbed his neck and wrists with Versace Eros, but he didn't feel the need to drown in it. A few minutes passed by and a porn star-ish girl stormed out of the office and slammed the door behind her.

A minute or two ticked by and Hilary came back out briskly saying, "Mr. Gilbert, Mr. Salvatore will see you now."

His heart started to pound and he did his best to reign it in and stood up with confidence. Hilary smiled and held the door open for him, allowing him to pass through before closing it. Jeremy's first glace of Mr. Salvatore was him rising from his seat. That black hair was pushed back away from his face showcasing his eyes.

"I tell her to send me someone qualified and she sends me a baby. Damon Salvatore," he quipped, holding out his hand.

"I'm 23, sir. Jeremy Gilbert, thank you for seeing me," greeted Jeremy, shaking his hand.

The comment threw him off a little, but he decided to roll with it.

"Pleasure, have a seat," he replied, sitting down at his desk and shuffling through papers.

Jeremy sat down in the black leather chair and observed that the room had a view of the city from the huge window. The best part of the office was the plush sofa and a liquor table beside it filled with bottles of brown liquors.

"So, you went to UVA and majored in marketing. Why are you here when marketing and advertising are not one and the same?" he questioned, glancing up from his papers.

"Marketing is how you promote the product and package it and target the product to the right audience. It provides the research necessary to effectively advertise the product," answered Jeremy, hoping the answer would be satisfactory.

"Then, why not apply to as an account executive, copy writer or another ad related position? Why would you want to be my secretary?" he fired back.

"I don't have enough experience to land one of those. Working for you would the best way for me to learn everything. I'm interested in the art side and you're the best creative director in the state," said Jeremy, trying not to blush.

"Glad to know I'm known. But, how do I know you won't be sneaking off to art department every day when I need you?"

"If I could eventually move to a position there it would be amazing. But, I'm here to work for you and be everything you need," responded Jeremy, not sure if he was talking about the job anymore.

"Thank you, stop by and see Hilary on your way out," he said, turning his eyes back to his papers.

"Yes sir," nodded Jeremy, thinking that had been the shortest interview he ever had. Where had he gone wrong? He rose from his seat and departed the office, wondering why he had to see Hilary. When he got back to the reception area, Hilary was herding the other applicants out.

"Thank you for coming. We'll call you back in if another secretarial position becomes available."

Wait, did that mean he actually got the job?

"Mr. Gilbert, come with me," she said, with a relieved smile and lead him down the hallway.

He recalled the jab Damon made about having someone come in with the right qualifications which meant Hilary must have caught some heat for the porn star ish girl. She led him into a conference style room and laid a stack of papers in front of a chair.

"Congratulations, you got the job and Mr. Salvatore was very impressed with you. If you choose to accept the position, it's full time and I need you signature on a few things."

"Wow, thank you. What is the pay?"

"It's a one year contract which can be extended. It starts out at 70k. All of our positions are under contract except for the freelance workers. Ms. Height is our head of human resources, but she's on vacation. I'm the office manager and filling in. If you have any questions I can't answer, feel free to ask her when she returns next week. Unfortunately, you have to be with us for a year before we offer health insurance. There are plenty of urgent care clinics in the area that are reasonable. You do have a few sick days if something serious happens. The most important part is the non disclosure agreement. Most agencies have them to protect their ideas if employees leave. We can sue if you go to another agency to work and tell our secrets. Sign the highlighted portions and then we'll discuss your job," she explained, passing him a pen.

He hardly ever got sick so him not having health insurance wasn't that big of a deal. However, actually having a contract and being guaranteed a job floored him.

"Hilary, I'm not from the area. Is there any way you can help me find a furnished apartment?" he asked, as he signed his name.

"Sure, the company has a realtor. I'll give her a call and have her set up some showings for you. You'll start at the beginning of next week at 8 a.m. I recommend getting here a tad bit earlier as Mr. Salvatore likes to be briefed on his way in. Basically, you take his coat and store it in the coat room. You'll bring his coffee to him and ask what he needs. He may tell you to hold his calls if he goes out or he might be looking for a particular call and tell you to put it right through. In the case of his wife, there may be times he doesn't want to talk to her. In that case, you tell her he's in a meeting and ask if you can take a message. If for some reason, he leaves the office and doesn't go home.. never tell his wife where he really went. It's all business and you aren't to be involved. Be sure to follow his instructions on whatever way he wants to deal with it. She needs a lot of attention and there are times when he needs a break from her. Dress is business casual. What you have on is good, no jeans or sneakers. Always be courteous and professional with clients or other co workers that need to see him. You are the only thing that stands between him and people he doesn't want to see. Come with me and I'll show you the phone and other equipment."

She gathered up his paper work and slid it into a file folder. He followed her to te desk in front of Mr. Salvatore's office and she went through how everything worked. He shouldn't have been surprised his boss was straight and married. Even though he didn't have a chance romantically, he had a chance to learn from the best. With that thought in mind, he sucked it up and prepared himself to succeed at his job.


End file.
